A California Girl's Guide to Dating in Chicago (pt. 1)

A Girl's Guide by Alessia

because I'm getting to know Chicago this week, I asked Ms. Alessia to share what she's learned about weathering the dating game in The Windy City. She's one of those girls who just get's it when it comes to dating. She has whip-sharp wit and complete composure (not to mention, she was probably one of the coolest girls at our college.). Here's a few of her secrets ...

Let's generalize ... California Guys vs. Chicago Guys: 

There is something about the Midwest that produces men of a more gentlemanly demeanor. In Orange County, I’d be lucky if a guy opened the door and didn’t suggest splitting the check. I’ve never experienced anything like that in Chicago. Generally, the men out here are much more chivalrous and well-mannered. And dare I say -- men out here are much manlier, with this corn-fed, All-American brand of swagger.

SoCal guys are typically too laidback about everything in life – jobs, chivalry, showering – and I really like the sense of urgency and hustle that men out here have. They’re athletic and professionally motivated. They’ll take you to a steakhouse on a first date instead of a taco joint. Don’t get me wrong, I like Rubio’s as much as the next California girl, but not when someone should be trying to win me over.

So for lots of reasons, Chicago has been a breath of fresh air.

So, a boy asks you out. This guy is probably not your soulmate but he's also probably not a psychopath. Do you say yes? 

I originally wrote this guest post in November when I was single. I met my boyfriend, J, only two weeks later. Reading the original now makes me laugh, but it still holds true. Here was my answer six months ago:
 “Quantity vs. quality -- the age old question. For me, the answer depends on how many irons I've got in the fire at any given time. I think you generally know right away if a guy is Mr. Right or Mr. Right Now, so if the former shows up -- I'm going all in for quality and the rest of the hopefuls can hit the bricks. But if winter is approaching, like it is now, and I'm not sold on anyone in particular, like I'm not now, then I'll likely date as many decent guys as I can reasonably manage, and quantity is the name of the game.”
The best part about reading that again is realizing that the above mentality put an amazing guy right in front of me. (It’s worth mentioning that when J and I met, I was on the biggest hot streak of my life.)

I’m a firm believer in not going out looking for the right guy. Live your life and be you. Date everyone and anyone you feel like. You're doing what makes you happy, so it doesn't matter if Mr. Right ever shows up. But when he does - quality always trumps quantity.

What's the key weathering the dating game in The Windy City? 

A GOOD SENSE OF HUMOR. Though I think that's true no matter where you're living and where you're dating. You're going to kiss a hell of a lot of frogs before you find that prince, and you can't take the journey too seriously or you'll need a second job just to pay for therapy. (I could go into some of the literally unbelievable experiences that I've had dating, but I'm saving those for a book and can't be giving out my material for free.)

Thinking back to my long single tenure, I’m glad that I wouldn’t settle for any of the “just okay” guys because it’s paid dividends. Sure, J and I go through our ups and downs. We recently had a rough patch, and i was feeling really confused and I didn't know if we'd make it through.

Then I went over to his new apartment while his parents were there, whom I adore. They were moving him in and J was putting together furniture in this tight shirt, all sweaty, and he looked amazing. Not to sound like Danielle Steele or anything, but in that moment I took inventory. I thought to myself, “Jesus, Alessia. You are dating the hottest man you have ever laid eyes on. You adore his family. He’s smart. He’s funny. He cares for you. He’s handy! You have so much in common. Don’t let stress get the best of you or the relationship.”

A good sense of humor is crucial to dating, and it’s crucial once you meet that great guy, too. You always have to be able to laugh and bring yourself back down to earth.

Alessia does Public Relations by day, and serves drinks by night. She is a Southern California expatriate and a newly minted catholic. She blogs at Un Giorno Da Leone and tweets here. She went on 12 first dates last year before finding the one

this is part 1 of 2 : A California Girl's Guide to Dating in Chicago
it is the fifth installment of the feature A Girl's Guide


  1. I heart Chicago so much. Good to know the guys live up to the place. I might argue that Norcal guys exhibit some of these same Chicago-guy characteristics...lots of hustle and swagger...but not many manners, I'll admit that.

    1. Sarah, I totally agree! Norcal is a different kind of California Man (I adore the skinny-jean wearing San Francisco variety). Alessia is from Orange County ... a whole 'nother world.

  2. I’ve been looking for a really good online dating site for some time, but they are not that good with many fake people, and I found globogirls.com, it's actually more of a social network thing for people who would like to meet travel mates from different countries. The good thing about it is that it's totally secure because they have the feature of video chatting with these girls so you'll not share your personal contacts unless you're 100% sure , One thing that I really liked was the tips on how to avoid scam and fraud.


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